US12275698B2 - Method of preparing diester-based material - Google Patents

Method of preparing diester-based material Download PDF

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Publication number
US12275698B2
US12275698B2 US17/635,925 US202117635925A US12275698B2 US 12275698 B2 US12275698 B2 US 12275698B2 US 202117635925 A US202117635925 A US 202117635925A US 12275698 B2 US12275698 B2 US 12275698B2
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reactor
reaction unit
reaction
alcohol
diester
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US20220371984A1 (en
Inventor
Jae Hun Jeong
Sung Kyu Lee
Yeon Uk CHOO
Song Hoon LEE
Hyoung JUN
Yun Gon HEO
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LG Chem Ltd
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LG Chem Ltd
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Assigned to LG CHEM, LTD. reassignment LG CHEM, LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CHOO, YEON UK, HEO, Yun Gon, JEONG, JAE HUN, JUN, Hyoung, LEE, SONG HOON, LEE, SUNG KYU
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/80—Phthalic acid esters
    • C07C69/82—Terephthalic acid esters

Definitions

  • the present invention relates to a method of preparing a diester-based material, and more particularly, to a method of preparing diester-based material which may improve productivity of a diester-based material by controlling a reaction rate of a reactant while minimizing an amount of energy used which is supplied to a reactor when continuously preparing a diester-based material.
  • the dicarboxylic acid may include one or more selected from the group consisting of, for example, aromatic polyvalent carboxylic acids such as phthalic acid, isophthalic acid, terephthalic acid, and trimellitic acid; and saturated or unsaturated aliphatic polyvalent carboxylic acids such as adipic acid, sebacic acid, azelaic acid, succinic acid, maleic acid, and fumaric acid.
  • aromatic polyvalent carboxylic acids such as phthalic acid, isophthalic acid, terephthalic acid, and trimellitic acid
  • saturated or unsaturated aliphatic polyvalent carboxylic acids such as adipic acid, sebacic acid, azelaic acid, succinic acid, maleic acid, and fumaric acid.
  • the dicarboxylic acid may be terephthalic acid.
  • the alcohol may be monohydric alcohol having 4 to 13, to 12, or 6 to 10 carbon atoms.
  • the monohydric alcohol may include linear chain or branched chain alcohol such as n-butyl alcohol, iso-butyl alcohol, secondary butyl alcohol, n-pentyl alcohol, n-hexyl alcohol, n-heptyl alcohol, n-octyl alcohol, 2-ethylhexyl alcohol, iso-octyl alcohol, iso-nonyl alcohol, n-nonyl alcohol, iso-decyl alcohol, n-decyl alcohol, undecyl alcohol, and tridecyl alcohol.
  • the alcohol may be 2-ethylhexyl alcohol.
  • the alcohol may be supplied to the reactor in an excessive amount relative to a stoichiometric amount required for a reaction with the dicarboxylic acid.
  • a mole ratio between the dicarboxylic acid and the alcohol supplied to the reactor 11 of the first reaction unit 10 may be 1:2 to 1:5 or 1:2 to 1:4.5.
  • Dicarboxylic acid and alcohol are supplied as reactants to the reactor 11 at a mole ratio in the range, thereby controlling a forward reaction rate of esterification while minimizing an amount of steam used to facilitate reaching a desired conversion rate.
  • the alcohol may be further supplied to any one or more of reactors of the reaction units from the second reaction unit 10 to the nth reaction unit n 0 .
  • the catalyst may include one or more selected from the group consisting of, for example, acid catalysts such as sulfuric acid, paratoluenesulfonic acid, and methanesulfonic acid; alkyl titanate catalysts such as tetraisopropyl titanate, tetrabutyl titanate, and tetra-2-ethylhexyl titanate; and organic metal catalysts such as dibutyl tin oxide and butyl tin maleate.
  • an organic titanium compound represented by alkyl titanate may be used as the catalyst, which increases an esterification rate to shorten a reaction time.
  • An operating temperature of the reactor may be, for example, 130° C. to 250° C., 140° C. to 250° C., or 150° C. to 230° C.
  • the operating temperature of the reactor may refer to the temperature of each reactor in the reaction units from the first reaction unit to the nth reaction unit. More specifically, each reactor in the reaction units from the first reaction unit to the nth reaction unit may be controlled identically or separately in the temperature range.
  • An operating pressure of the reactor may be ⁇ 1 kg/cm 2 G to 5.5 kg/cm 2 G, 0 kg/cm 2 G to 4.5 kg/cm 2 G, or 0 kg/cm 2 G to 4 kg/cm 2 G.
  • the operating pressure of the reactor may refer to the pressure of each reactor in the reaction units from the first reaction unit to the nth reaction unit. More specifically, each reactor in the reaction units from the first reaction unit to the nth reaction unit may be controlled identically or separately in the pressure range.
  • the dicarboxylic acid may be terephthalic acid and the alcohol may be 2-hetylhexyl alcohol.
  • dioctyl terephthalate DBP
  • the dioctyl terephthalate which is a material which is widely used as an environmentally friendly and non-toxic plasticizer, has excellent compatibility with a polymer material such as PVC and excellent properties of low volatility and electrical properties.
  • the reaction part has a total of n reaction units connected in series, and may be designed considering conversion rate control of the reaction and a residence time in each unit reaction and the composition of a product to be achieved.
  • n may be 2 to 8, 3 to 7, or 4 to 6, that is, the reaction part may include 2 to 8, 3 to 7, or 4 to 6 reaction units.
  • a reaction unit 10 , 20 , 30 , 40 , 50 , or n 0 may further include: a column 12 , 22 , 32 , 42 , 52 , or n 2 which is supplied with an upper discharge stream from a reactor including alcohol and water vaporized during esterification from a reactor 11 , 21 , 31 , 41 , 51 , or n 1 to perform gas-liquid separation, passes a gas phase through a condenser 13 , 23 , 33 , 43 , 53 , or n 3 as an upper discharge stream to be supplied to a layer separator 14 , 24 , 34 , 44 , 54 , or n 4 , and supplies a liquid phase to the reactor 11 , 21 , 31 , 41 , 51 , or n 1 as a lower discharge stream; and a layer separator 14 , 24 , 34 , 44 , 54 , or n 4 which performs a separation into a water layer and an alcohol layer
  • the diester-based material as a reaction product and water as a by-product involved in esterification may be produced by esterification of dicarboxylic acid and alcohol.
  • the reaction product of the esterification may include the diester-based material, water, and an unreacted material.
  • water as a by-product should be effectively removed to prevent a reverse reaction and catalyst deactivation by water.
  • water is vaporized and discharged.
  • alcohol having a similar boiling point to water is also vaporized together, and the vaporized alcohol may be recovered and refluxed again to the reactor to maintain the concentration of the reactant high and water may be removed.
  • alcohol participates in the reaction, but alcohol which does not participate in the reaction and is vaporized due to esterification at a higher temperature than the boiling point of alcohol is inevitably present, and simultaneously, water occurs as a by-product in addition to the diester-based material as a reaction product and water may be vaporized with alcohol and discharged as the upper discharge stream from the reactor.
  • the vaporized water and alcohol are discharged as the upper discharge stream of the reactor and may be supplied to the column.
  • gaseous alcohol and water introduced from the reactor may be liquefied by liquid alcohol at a low temperature supplied from the layer separator to an upper portion of the column, most of the gaseous alcohol is selectively liquefied and discharge as the lower discharge stream from the column, the lower discharge stream from the column including the liquid alcohol is introduced again to the reactor, and the liquid alcohol may participate in the esterification again.
  • the upper discharge stream from the reactor through the column, water included in the upper discharge stream from the reactor is condensed and introduced to the reactor again, thereby improving a forward reaction rate.
  • alcohol vaporized from the reactor is refluxed to the reactor again, thereby maintaining an excessive amount ratio of alcohol in the reactor, and water as the by-product of esterification is discharged to the outside of a reaction system and removed, thereby preventing reflux of water to the reactor to prevent a reaction rate reduction and catalyst performance deterioration in the reactor.
  • gaseous water and unliquefied gaseous alcohol in the column are discharged as the upper discharge stream from the column, and the upper discharge stream from the column passes through the condenser to be supplied to the layer separator.
  • the layer separator is equipment for layer-separating liquid alcohol and water, and at this point, gaseous alcohol and water need to be liquefied in the layer separator or before being introduced to the layer separator.
  • a condenser is installed in an arbitrary area of a line where the upper discharge stream from the column is transferred to the layer separator, and heat of gaseous alcohol and water is removed by the condenser, thereby liquefying alcohol and water before being introduced to the layer separator.
  • dicarboxylic acid and alcohol are esterified in the reactor of the first reaction unit to prepare a reaction product, and a lower discharge stream including the reaction product may be supplied to the reaction unit at the rear end through a lower discharge line.
  • the operating pressure of the reactor of the nth reaction unit may be equal to or lower than the operating pressure of the reactor of the n ⁇ 1th reaction unit.
  • the operating pressure of the reactor may be reduced from the first reaction unit 10 to the nth reaction unit n 0 .
  • the reactor 11 of the first reaction unit 10 is operated at high pressure and the operating pressure of the reactor is reduced toward the reaction unit at the rear end, thereby removing water well toward the reaction unit at the rear end to control the reaction rate of the reactant, so that a desired conversion rate may be reached in the reactor n 1 of the nth reaction unit n 0 at the rearmost end.
  • the reactor of the reaction unit to start pressure reduction among the reactors of the reaction units from the second reaction unit 10 to the nth reaction unit n 0 may be appropriately selected depending on the conversion rate.
  • the operating pressure of the reactor is controlled in each reaction unit, thereby minimizing a steam amount supplied to the reactor 11 of the first reaction unit 10 to reduce the amount of entire steam used, facilitating removal of water which is the by-product in the reactor of the reaction unit at the rear end to control the reaction rate, and facilitating reaching a desired conversion rate in the reactor n 1 of the nth reaction unit n 0 at the rearmost end.
  • the operating temperature of the reactor of the nth reaction unit may be equal to or higher than the operating temperature of the reactor of the n ⁇ 1th reaction unit.
  • the operating temperature may be sequentially increased from the first reaction unit 10 to the nth reaction unit n 0 .
  • the reactor 11 of the first reaction unit 10 is operated at high pressure and the operating temperature of the reactor is sequentially increased toward the reaction unit at the rear end, thereby controlling the reaction rate of the reactant in the reactor of each reaction unit.
  • the operating temperature of the reactor of the nth reaction unit may be increased by 0% to 20%, 0.1% to 15%, or 1% to 5%, as compared with the operating temperature of the reactor of the n ⁇ 1th reaction unit.
  • the reaction rate which is lowered due to a decrease in the reactant toward the reaction unit at the rear end is improved, thereby facilitating reaching a desired conversion rate in the reactor of the reaction unit at the rearmost end.
  • the operating pressure of the reactor n 1 of the nth reaction unit n 0 which is a reaction unit at the rearmost end may be ⁇ 1 kg/cm 2 G to 1 kg/cm 2 G, ⁇ 0.5 kg/cm 2 G to 0.5 kg/cm 2 G, or 0 kg/cm 2 G to 0.2 kg/cm 2 G, and the operating temperature thereof may be 200° C. to 250° C., 210° C. to 240° C., or 220° C. to 230° C.
  • the desired conversion rate is in a state of being reached, in which the content of the reactant is low, water as the by-product is present, and the content of the diester-based material as the product is high, and in this case, the operating pressure and the operating temperature are controlled within the range, thereby removing water as the by-product effectively and promoting the forward reaction to facilitate reaching a desired conversion.
  • devices such as a distillation column, a condenser, a reboiler, a valve, a pump, a separator, and a mixer may be further installed.
  • Example 2 The process was performed in the same manner as in Example 1, except that ASPEN PLUS available from Aspen Technology Inc. was used to simulate the preparation process of dioctyl terephthalate (DOTP) without setting the conditions to reach a conversion rate of 99%.
  • ASPEN PLUS available from Aspen Technology Inc. was used to simulate the preparation process of dioctyl terephthalate (DOTP) without setting the conditions to reach a conversion rate of 99%.
  • the temperature of each reactor from the reactor 11 of the first reaction unit 10 to the reactor 51 of the fifth reaction unit 50 was controlled while maintaining the temperature at 215° C.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US17/635,925 2020-11-17 2021-08-20 Method of preparing diester-based material Active 2043-04-13 US12275698B2 (en)

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KR1020200153956A KR102915059B1 (ko) 2020-11-17 2020-11-17 디에스터계 물질의 제조방법
KR10-2020-0153956 2020-11-17
PCT/KR2021/011084 WO2022108050A1 (ko) 2020-11-17 2021-08-20 디에스터계 물질의 제조방법

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EP (1) EP4023628B1 (de)
JP (1) JP2023507538A (de)
KR (1) KR102915059B1 (de)
CN (1) CN114829332A (de)
WO (1) WO2022108050A1 (de)

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KR102865300B1 (ko) * 2022-10-04 2025-09-26 한화솔루션 주식회사 에스테르계 조성물의 제조 방법

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KR20190027623A (ko) 2017-09-07 2019-03-15 주식회사 엘지화학 에스터 조성물의 제조 시스템 및 이를 이용한 에스터 조성물의 제조 방법
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KR102915059B1 (ko) 2026-01-19
KR20220067352A (ko) 2022-05-24
EP4023628B1 (de) 2025-12-24
JP2023507538A (ja) 2023-02-24
EP4023628A4 (de) 2023-09-20
WO2022108050A1 (ko) 2022-05-27
EP4023628A1 (de) 2022-07-06
CN114829332A (zh) 2022-07-29
US20220371984A1 (en) 2022-11-24

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